


Perfect

by TheatricArcana



Category: Critical Role (Web Series)
Genre: First Time, LIGHT body worship, M/M, Penis In Vagina Sex, Smut, Trans Essek Thelyss, Trans Male Character, Vaginal Fingering, Vaginal Sex, What's sexier than wizards? Premature Ejaculation, i think???
Language: English
Status: Completed
Published: 2020-07-31
Updated: 2020-07-31
Packaged: 2021-03-05 19:40:27
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,318
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25630708
Author URL: https://archiveofourown.org/users/TheatricArcana/pseuds/TheatricArcana
Summary: "Caleb's hands were shaking when he grabbed Essek's waist to pull him closer. He felt like he was a teenager again- fumbling around and trying to figure out what he was doing- and he hadn't felt like that since he had actually been a teenager. To say it had been a while would be an understatement."Aka: Caleb, very excited to take care of his lover and give Essek an amazing first time, works himself up a little too hard and ends the sex a lot faster than he would like to. Essek takes it well enough. (Check notes at the beginning for warnings!)
Relationships: Essek Thelyss/Caleb Widogast
Comments: 9
Kudos: 132





	Perfect

**Author's Note:**

> I just wanted to write some smut that wasn't super serious! I don't write or post fanfics very often, so if you have any criticism please take it easy because I'm a baby.
> 
> Essek is written as transmasculine (the author is also transmasculine), but he experiences minimal dysphoria. There is a section of the fanfic dedicated to Caleb being REALLY into Essek's breasts and they are talked about in detail. I also used words such as cunt/clit to describe Esseks anatomy. If you think any of that may make you uncomfortable, I advise you not to read. Otherwise, I hope you enjoy these gay wizards doing gay shit! :)
> 
> EDIT: I meant to include this earlier, but in case you're wondering why Essek is so short compared to Caleb: The players handbook says that Elves are shorter than humans on average, and that Drow are even smaller on average compared to other subraces of Elves. So I think it would logically work out that Essek is short while not floating. Also I'm 5'2 so just let me have this LMAO

Caleb's hands were shaking when he grabbed Essek's waist to pull him closer. He felt like he was a teenager again- fumbling around and trying to figure out what he was doing- and he hadn't felt like that since he had _actually_ been a teenager. To say it had been a while would be an understatement.

Essek, to be fair, didn't have much experience under his belt either. Similar to Caleb, he had spent much of his youth studying the arcane, but Essek didn't have the luck of finding any friends- or a lover- to keep him company like Caleb did. Nowadays, Essek also had an image to maintain. He couldn't be caught fooling around with someone without it damaging his carefully crafted image. With a reputation to uphold and so many more important things to focus on in his life, Essek had always put romance, intimacy, and sex on the back burner.

Until Caleb came along, that is.

Caleb settled between Esseks legs, leaning over Essek to softly kiss him again. Essek grinned against Caleb's lips as he spread his legs even wider to accommodate Caleb between them. Essek was still shaking slightly as he returned the kiss, which had concerned Caleb earlier until Essek admitted that he was just shaking from the adrenaline rush that came with having sex for the first time.

Caleb was so excited and impatient that he could barely contain himself, but he forced himself to slow down before he overwhelmed Essek. Caleb remembered just how nervous Essek had been earlier when he had first gotten Essek undressed. Essek had been such a confident and somewhat intimidating figure when they had first met, which is what made it so surprising- and endearing- when Caleb realized Essek was actually somewhat shy when he took his clothes off.

Caleb could see why- the cloak and mantle combined with the hovering added bulk and height to his presence. It was a carefully crafted appearance that made Essek not only look, but also _feel_ more confident and powerful then he would normally. Caleb _would_ say that the cloak hid what Essek was lacking, but it felt inappropriate to imply in any way that Essek was _lacking_ anything.

True, Essek was smaller than Caleb had anticipated, but it wasn't something Caleb actually minded. Caleb hadn't been aware of Essek's short stature when they first met- in fact, he had actually thought that Essek was tall compared to the average Drow- but now he knew that Essek had only been that tall because he had been floating several inches above the ground.

Essek hovering to make himself appear tall despite his actual height was for good reason, though. When Essek wasn't hovering, he barely passed Caleb's shoulders. Trying to gain the respect of other powerful figures, from both his own government and foreign ones, would be much harder if they all had to look down at Essek.

Caleb still wouldn't call him _lacking_ for being short, though. Essek had a million other things he _didn't_ lack, or things he had in excess that more than made up for it.

For starters, Essek was excessively handsome. _Beautiful_ , even. He also had a wit matched to Caleb's own, and a body that Caleb could only think to describe as perfect. And rest assured, Caleb had _definitely_ taken his time soaking in the view of Essek, naked and sprawled out beneath him. The only word that had come to mind the entire time was "Perfect".

Stunning white freckles were speckled all over Esseks smooth, dark skin. It resulted in Essek looking like the most beautiful night sky that Caleb had ever laid eyes on. Essek had features that were truly fitting for a god if you were to ask Caleb. Perfect eyes, perfect hair, perfect jawline, perfect _everything_. Even when Caleb let his eyes start to travel downward, everything stayed perfect in its own way.

For example, Esseks chest.

Caleb didn't say anything or move to touch. He wasn't fully aware of how Essek felt about his body in some areas, including his chest, but Caleb would be lying if he said he didn't have to bite back a few comments on how much he loved Esseks breasts.

He couldn't help but stare for a few seconds, and it was a few seconds too long, because when Caleb looked up again, Essek was watching him curiously.

Caleb flushed bright red and muttered an apology when he realised he had been caught openly staring at Esseks tits. He could only hope that he hadn't made Essek uncomfortable.

Essek broke the silence.

"...Do you want to touch them?" Essek asked, almost casually, but there was still a hint of nervousness in his voice.

Calebs mouth fucking _watered_ despite his hesitation.

"It… doesn't make you uncomfortable?" Caleb wanted to touch, _very_ bad, but he didn't want to do anything that would make Essek uncomfortable. Caleb hated the thought that Essek may be offering just because he could tell that Caleb wanted it, even though it might make Essek uncomfortable if he actually accepted the offer.

Essek, however, responded to Caleb's question by grabbing one of Caleb's hands and placing it over one of his breasts for Caleb.

Caleb's breath hitched and he reflexively grabbed onto the soft skin- gently, not enough to cause Essek any pain or discomfort- but he simply couldn't stop himself. He wanted to know what every inch of Esseks body felt like.

" _You_ never make me uncomfortable, Mr. Widogast."

Esseks breasts were small, barely enough for Caleb to even consider them "handful", but they were soft and perky and perfectly suited for Esseks body. For once, not thinking before speaking actually helped Caleb. Caleb was so distracted by Essek that he was speaking Zemnian out of habit, which was good because he found the compliments pouring out of his mouth before he could even think to stop himself.

" _Du bist schön_ "

" _Du bist so perfekt für mich, meine Liebe_ "

" _Deine Titten sind_ wunderschön"

The compliments got progressively filthier as he went on. He muttered them between open-mouthed kisses and gentle nips, most of which were centered around or on Esseks chest.

Essek never expressed discomfort, but his cheeks were flushed a beautiful shade of purple by the time Caleb stopped talking. Essek didn't really understand what Caleb was saying, but he had learned a few Zemnian words from being around Caleb, and the few words that he recognized were enough for Essek to get the gist of what Caleb was saying without asking for a translation.

Essek couldn't meet Caleb's eyes. Instead, he opted to bury his face into one of the nearby pillows as Caleb rambled on. One of Caleb's hands softly kneaded and massaged Esseks breast (Which probably did more for Caleb than Essek, as Essek didn't necessarily derive physical pleasure from simply having his chest touched, but _God's_ Caleb could not resist the urge to touch) while his other hand moved between Essek's thighs. Two of his fingers slid inside of Essek easily as his thumb rubbed little circles on Essek's engorged clit.

This went on for a while. Caleb would mutter the filthiest things about Essek that he could think of in Zemnian, and Essek would moan and gasp at the feeling of Caleb's fingers working him. Caleb almost wanted to make Essek climax again just like this, but he was painfully aware of the erection straining against his shorts, and he couldn't find it in himself to delay his relief any longer. He _needed_ to be inside of Essek. He had spent plenty of time making sure Essek was warmed up by now, so there was really no reason to wait any longer. If he didn't act soon, the anticipation alone was going to kill Caleb before he even had a chance to properly fuck Essek.

Caleb let go of Essek's chest so he could hastily remove his briefs (which was quite the challenge with just one hand, but Caleb made it work) and line himself up while still being able to continue his affections towards Esseks clit. Esseks gasps and sighs were muffled into the pillow, but Caleb could still hear them if he listened closely.

"Ready?"

Essek lifted his head away from the pillow that he had buried his face into so that he could look at Caleb.

"H- _ah_ \- How am I supposed to know?" Essek let out a breathless laugh, which turned into a loud moan as Caleb slid a third finger inside of him.

"Does this feel uncomfortable?" Caleb asked, gently thrusting and then spreading his fingers inside of Essek ever-so-slightly. Essek's thighs quivered for a second before he got them under control again.

"N-No." Essek gasped out, and then "I want you in me."

Caleb choked back a groan upon hearing Essek say that. Essek, the polite and well-behaved Shadowhand, was coming apart under him and asking for Caleb to fuck him. It was almost too much.

With a surprisingly minimal amount of fumbling, Caleb slid his fingers out of Essek and lined himself up with Esseks entrance. Caleb tried to focus on Esseks face so he could monitor Essek for any discomfort, but he may as well have gone blind with pleasure the second he pressed his cock into Essek. Caleb could not possibly begin to describe all the sensations he felt.

Essek was _everything_ in that moment.

Essek still looked perfect. His mouth hung open in a perfect little 'o' shape as he felt Caleb slowly push into him. His fine, white hair spread out on the pillow beneath his head looked like a halo. His ears, cheeks, and even his shoulders and chest were flushed purple. He looked like the most beautiful painting Caleb had ever seen, except he was here and real and underneath and _around_ Caleb. Caleb could tell he was real and not just a painting, too, because Essek was-

Essek was-

Oh G _ods._

Essek was _impossibly_ tight and hot around Caleb's cock. He could feel how slick and warm Essek was inside, all for Caleb, all _because_ of Caleb. Essek's cunt involuntarily clenched as Caleb bottomed out inside of him. It was _so_ good. He had been wanting this for so long, and now that he had it, it was entirely too much.

Caleb leaned over Essek entirely and buried his face into Essek's neck, a strangled moan leaving his mouth as he came _hard_ inside of Essek.

Caleb came.

Caleb came less than twenty seconds after being inside of Essek.

_Fuck._

Even when he had been a teenage virgin and had sex with Astrid for the first time, he had _not_ cum humiliatingly quickly like that. It had been a long time since Caleb had gotten to indulge himself in physical pleasures, but this? This was _embarrassing._

"Oh my _Gods_." Caleb groaned, in a way that sounded less pleasurable and more disappointed and frustrated. Essek picked up on the tone change quickly.

"Are you okay?" Essek sounded confused and concerned, meaning he didn't connect the dots as to what just happened. Caleb wished for nothing more than to be buried alive at the moment, but he figured he owed Essek an explanation on what was going on.

"I just… came…" Caleb muttered, not even lifting his head to look at Essek.

There was a moment of silence.

Then Essek started _laughing._

Essek couldn't help it. It was funny. They were supposed to have a hot, steamy first time together and Caleb came within twenty seconds of being inside of him.

"Oh my _Gods_ , that's so embarrassing." Caleb complained, but Essek only laughed harder, and his laughter was oddly infectious. Despite himself, Caleb couldn't help but start to laugh as well.

"It's fine, I'll take it as a compliment." Essek said between giggles, and Caleb wanted to _strangle_ Essek for _laughing at him_ when he was so obviously embarrassed, but he was simultaneously relieved that at least Essek wasn't disappointed or upset. There wasn't any tension in Essek's reaction. It could have been worse.

Caleb pulled out of Essek dejectedly, having gone soft already. Caleb was pretty sure he was more disappointed than Essek was, as Essek was still fighting off fits of laughter when Caleb reached over to grab a rag to clean up any mess that may get on the sheets. Caleb could not _believe_ that he had actually just done that.

Caleb tossed the rag to the side when he was done cleaning the mess, and Essek's laughter finally died down. Caleb found himself staring at the wall for a few seconds, unable to prevent himself from replaying the night's events in his head, leading to another wave of embarrassment.

Essek had assured Caleb multiple times that the concept of "Virginity" was not something that Xhorhasians gave any importance to, or even had a concept of to begin with, but that didn't change the fact that this was supposed to be Esseks first time and that it should have been special. Instead, Caleb had gotten over excited and came in record time.

"Caleb?" Essek's voice pulled Caleb away from his souring thoughts.

Essek was still smiling, but it wasn't an amused smile anymore- It was content and fond. Caleb couldn't help but return the look.

Essek extended a hand to Caleb from where he was lying on the bed, and Caleb was smart enough to understand that Essek was trying to invite him closer without speaking.

Caleb took Essek's hand and let Essek pull him closer. They settled onto the bed in a familiar tangle of limbs, only this time there was no clothing to seperate them like there usually was. It definitely felt more intimate like this, and Caleb found himself thoroughly distracted from his feelings of embarrassment simply by being in Essek's presence.

"You can eat me out again later tonight to make up for it."


End file.
